[Li+].[Br-].[CH3:3][C:4]1([O:7][CH2:6]1)[CH3:5].F[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[N:18]1[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1.[C:24](OCC)(=O)C>CN1C(=O)CCC1.O>[CH3:3][C:4]([OH:7])([CH3:5])[CH2:6][NH:23][C@@H:20]1[CH2:21][CH2:22][N:18]([C:10]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=2[CH3:24])[CH2:19]1LiBr (153.6 mg) and isobutylene oxide (85.1 mg) were added to a solution of (R)-1-(2-fluoro-4-nitro-phenyl)-pyrrolidin-3-ylamine (100 mg) in NMP (2 mL) and the reaction mixture was heated for 2 d at 80° C. Then ethyl acetate and water were added to the mixture. The aqueous phase was extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 297.15 (C14H20FN3O3); MS (ESI): 298 (M+H+).
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